#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:23:37 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178897 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/26/4112604.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4112604
loop_
_publ_author_name
'Joseph M. Keane'
'Mahendra D. Chordia'
'Christopher J. Mocella'
'Michal Sabat'
'Carl O. Trindle'
'W. Dean Harman'
_publ_section_title
;
 Transition Metal-Stabilized Arenium Cations: Protonation of Arenes
 Dihapto-Coordinated to π-Basic Metal Fragments
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6806
_journal_page_last               6815
_journal_paper_doi               10.1021/ja039824h
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C21 H24 B N8 O2 Re'
_chemical_formula_weight         617.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.285(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2750(10)
_cell_length_b                   12.9206(10)
_cell_length_c                   14.7993(12)
_cell_measurement_reflns_used    7277
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      32.486
_cell_measurement_theta_min      2.678
_cell_volume                     2215.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30064
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    5.522
_exptl_absorpt_correction_T_max  0.801924
_exptl_absorpt_correction_T_min  0.653847
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            greenish
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.480
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         8013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0328P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                6480
_reflns_number_total             8013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja039824hsi20040325_025335.cif
_cod_data_source_block           C21H24BN8O2Re
_cod_database_code               4112604
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
Re Re 0.434122(8) 0.170528(8) 0.197223(7) 0.01755(3) Uani 1 1 d
O1 O 0.7067(2) 0.2120(2) 0.11552(17) 0.0387(5) Uani 1 1 d
O2 O 0.42623(19) -0.03549(16) 0.09852(16) 0.0311(5) Uani 1 1 d
N1 N 0.4306(2) 0.31996(17) 0.27230(17) 0.0205(4) Uani 1 1 d
N2 N 0.3400(2) 0.33845(17) 0.30407(16) 0.0213(4) Uani 1 1 d
N3 N 0.25179(19) 0.19852(18) 0.13083(16) 0.0198(4) Uani 1 1 d
N4 N 0.18699(18) 0.23893(17) 0.18078(16) 0.0196(4) Uani 1 1 d
N5 N 0.37325(19) 0.10507(17) 0.30507(16) 0.0209(4) Uani 1 1 d
N6 N 0.2947(2) 0.15547(17) 0.33554(17) 0.0220(5) Uani 1 1 d
N7 N 0.43874(19) 0.25385(18) 0.07321(17) 0.0217(5) Uani 1 1 d
N8 N 0.4403(2) 0.2863(2) -0.07250(17) 0.0257(5) Uani 1 1 d
C1 C 0.6805(2) 0.1435(3) 0.1753(2) 0.0279(6) Uani 1 1 d
C2 C 0.7104(3) 0.0420(3) 0.1848(2) 0.0313(7) Uani 1 1 d
C3 C 0.6929(3) -0.0162(3) 0.2613(3) 0.0351(7) Uani 1 1 d
C4 C 0.6441(3) 0.0271(3) 0.3218(2) 0.0327(7) Uani 1 1 d
C5 C 0.6023(3) 0.1330(3) 0.3096(2) 0.0265(6) Uani 1 1 d
C6 C 0.6219(2) 0.1928(2) 0.2346(2) 0.0262(6) Uani 1 1 d
C7 C 0.7759(3) 0.1737(4) 0.0619(3) 0.0463(10) Uani 1 1 d
C8 C 0.3503(3) 0.4337(2) 0.3434(2) 0.0271(6) Uani 1 1 d
C9 C 0.4497(3) 0.4779(2) 0.3394(2) 0.0331(7) Uani 1 1 d
C10 C 0.4975(3) 0.4047(2) 0.2948(2) 0.0277(6) Uani 1 1 d
C11 C 0.0780(2) 0.2530(2) 0.1220(2) 0.0230(5) Uani 1 1 d
C12 C 0.0708(2) 0.2214(2) 0.0316(2) 0.0260(6) Uani 1 1 d
C13 C 0.1806(3) 0.1875(2) 0.0403(2) 0.0250(6) Uani 1 1 d
C14 C 0.2645(3) 0.0945(3) 0.3978(2) 0.0293(6) Uani 1 1 d
C15 C 0.3249(3) 0.0037(3) 0.4089(2) 0.0339(7) Uani 1 1 d
C16 C 0.3913(3) 0.0135(2) 0.3496(2) 0.0290(6) Uani 1 1 d
C17 C 0.4523(2) 0.2138(2) -0.0048(2) 0.0238(5) Uani 1 1 d
C18 C 0.4177(3) 0.3786(3) -0.0359(2) 0.0345(7) Uani 1 1 d
C19 C 0.4161(3) 0.3575(3) 0.0531(2) 0.0311(7) Uani 1 1 d
C20 C 0.4469(3) 0.2697(3) -0.1680(2) 0.0337(7) Uani 1 1 d
C21 C 0.4301(2) 0.0451(2) 0.13674(19) 0.0205(5) Uani 1 1 d
B B 0.2428(3) 0.2590(3) 0.2893(2) 0.0226(6) Uani 1 1 d
H1B H 0.177(2) 0.288(2) 0.319(2) 0.016(7) Uiso 1 1 d
H2 H 0.744(3) 0.008(3) 0.138(2) 0.032(9) Uiso 1 1 d
H3 H 0.719(3) -0.086(3) 0.270(2) 0.033(9) Uiso 1 1 d
H4 H 0.643(3) -0.015(3) 0.385(3) 0.059(12) Uiso 1 1 d
H5 H 0.606(3) 0.168(2) 0.364(2) 0.023(8) Uiso 1 1 d
H6 H 0.636(3) 0.267(3) 0.243(2) 0.028(9) Uiso 1 1 d
H7A H 0.849(4) 0.136(3) 0.112(3) 0.057(12) Uiso 1 1 d
H7B H 0.733(4) 0.112(4) 0.014(3) 0.068(14) Uiso 1 1 d
H7C H 0.785(4) 0.236(4) 0.021(3) 0.076(15) Uiso 1 1 d
H8 H 0.295(3) 0.456(3) 0.364(2) 0.033(10) Uiso 1 1 d
H9 H 0.477(3) 0.536(3) 0.357(3) 0.034(10) Uiso 1 1 d
H10 H 0.561(3) 0.408(3) 0.279(2) 0.033(10) Uiso 1 1 d
H11 H 0.031(3) 0.278(2) 0.145(2) 0.016(8) Uiso 1 1 d
H12 H 0.012(3) 0.222(3) -0.025(2) 0.026(8) Uiso 1 1 d
H13 H 0.204(3) 0.161(2) -0.012(2) 0.017(8) Uiso 1 1 d
H14 H 0.212(3) 0.120(2) 0.425(2) 0.020(8) Uiso 1 1 d
H15 H 0.324(3) -0.054(3) 0.446(3) 0.043(11) Uiso 1 1 d
H16 H 0.440(3) -0.030(3) 0.335(2) 0.024(8) Uiso 1 1 d
H17 H 0.461(3) 0.146(3) -0.013(3) 0.047(12) Uiso 1 1 d
H18 H 0.400(3) 0.443(3) -0.073(3) 0.057(12) Uiso 1 1 d
H19 H 0.405(3) 0.404(3) 0.098(2) 0.034(9) Uiso 1 1 d
H20A H 0.501(4) 0.319(3) -0.176(3) 0.042(11) Uiso 1 1 d
H20B H 0.478(4) 0.198(3) -0.171(3) 0.053(12) Uiso 1 1 d
H20C H 0.378(3) 0.269(3) -0.210(3) 0.043(11) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C21 Re N7 91.71(10)
C21 Re N5 93.12(10)
N7 Re N5 161.45(9)
C21 Re N3 93.95(10)
N7 Re N3 80.95(8)
N5 Re N3 80.86(9)
C21 Re C6 95.44(11)
N7 Re C6 80.12(10)
N5 Re C6 117.17(11)
N3 Re C6 159.08(11)
C21 Re C5 92.31(11)
N7 Re C5 117.82(10)
N5 Re C5 79.87(10)
N3 Re C5 160.03(11)
C6 Re C5 37.74(12)
C21 Re N1 176.93(10)
N7 Re N1 90.13(8)
N5 Re N1 84.38(8)
N3 Re N1 83.91(8)
C6 Re N1 87.30(10)
C5 Re N1 89.01(10)
C1 O1 C7 116.5(3)
C10 N1 N2 105.8(2)
C10 N1 Re 135.8(2)
N2 N1 Re 118.34(16)
C8 N2 N1 109.8(2)
C8 N2 B 129.0(2)
N1 N2 B 121.2(2)
C13 N3 N4 106.2(2)
C13 N3 Re 132.2(2)
N4 N3 Re 121.55(17)
C11 N4 N3 109.7(2)
C11 N4 B 130.8(2)
N3 N4 B 119.5(2)
C16 N5 N6 106.4(2)
C16 N5 Re 132.3(2)
N6 N5 Re 121.17(17)
C14 N6 N5 109.3(2)
C14 N6 B 130.0(2)
N5 N6 B 120.2(2)
C17 N7 C19 105.4(2)
C17 N7 Re 126.6(2)
C19 N7 Re 127.7(2)
C17 N8 C18 107.3(3)
C17 N8 C20 126.3(3)
C18 N8 C20 126.3(3)
C2 C1 O1 125.6(3)
C2 C1 C6 122.1(3)
O1 C1 C6 112.2(3)
C1 C2 C3 118.9(3)
C4 C3 C2 121.4(3)
C3 C4 C5 121.6(3)
C6 C5 C4 117.5(3)
C6 C5 Re 69.98(16)
C4 C5 Re 119.9(2)
C5 C6 C1 118.3(3)
C5 C6 Re 72.29(17)
C1 C6 Re 118.4(2)
N2 C8 C9 108.6(3)
C8 C9 C10 105.1(3)
N1 C10 C9 110.7(3)
N4 C11 C12 108.6(3)
C11 C12 C13 104.9(3)
N3 C13 C12 110.6(3)
N6 C14 C15 108.8(3)
C14 C15 C16 104.7(3)
N5 C16 C15 110.9(3)
N7 C17 N8 111.2(3)
C19 C18 N8 106.2(3)
C18 C19 N7 109.8(3)
O2 C21 Re 179.0(2)
N2 B N6 109.3(2)
N2 B N4 108.5(2)
N6 B N4 107.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Re C21 1.844(3)
Re N7 2.145(2)
Re N5 2.147(2)
Re N3 2.157(2)
Re C6 2.204(3)
Re C5 2.235(3)
Re N1 2.235(2)
O1 C1 1.363(4)
O1 C7 1.429(4)
O2 C21 1.178(3)
N1 C10 1.343(4)
N1 N2 1.364(3)
N2 C8 1.350(4)
N2 B 1.534(4)
N3 C13 1.343(4)
N3 N4 1.357(3)
N4 C11 1.346(3)
N4 B 1.545(4)
N5 C16 1.336(4)
N5 N6 1.358(3)
N6 C14 1.354(4)
N6 B 1.541(4)
N7 C17 1.325(4)
N7 C19 1.380(4)
N8 C17 1.344(4)
N8 C18 1.375(4)
N8 C20 1.458(4)
C1 C2 1.357(4)
C1 C6 1.454(4)
C2 C3 1.433(5)
C3 C4 1.352(5)
C4 C5 1.451(4)
C5 C6 1.436(5)
C8 C9 1.367(5)
C9 C10 1.388(4)
C11 C12 1.374(4)
C12 C13 1.382(4)
C14 C15 1.368(5)
C15 C16 1.388(4)
C18 C19 1.351(5)
